CN104640892B - 含聚异氰脲酸酯的中间体材料 - Google Patents
含聚异氰脲酸酯的中间体材料 Download PDFInfo
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- CN104640892B CN104640892B CN201380038054.0A CN201380038054A CN104640892B CN 104640892 B CN104640892 B CN 104640892B CN 201380038054 A CN201380038054 A CN 201380038054A CN 104640892 B CN104640892 B CN 104640892B
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- Prior art keywords
- isocyanurate
- composition
- catalyst
- compound
- trimerization
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 118
- 239000011495 polyisocyanurate Substances 0.000 title claims abstract description 112
- 239000000203 mixture Substances 0.000 claims abstract description 156
- 238000000034 method Methods 0.000 claims abstract description 64
- 230000006641 stabilisation Effects 0.000 claims abstract description 21
- 238000011105 stabilization Methods 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims description 105
- 150000001875 compounds Chemical class 0.000 claims description 92
- 238000005829 trimerization reaction Methods 0.000 claims description 89
- 229920001228 polyisocyanate Polymers 0.000 claims description 55
- 239000005056 polyisocyanate Substances 0.000 claims description 55
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000012948 isocyanate Substances 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 25
- 229920000647 polyepoxide Polymers 0.000 claims description 24
- 239000003822 epoxy resin Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 17
- 230000008859 change Effects 0.000 claims description 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052700 potassium Inorganic materials 0.000 claims description 14
- 239000011591 potassium Substances 0.000 claims description 14
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
- 230000007613 environmental effect Effects 0.000 claims description 11
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical group [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 10
- 239000004593 Epoxy Substances 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 9
- 230000000996 additive effect Effects 0.000 claims description 9
- 150000004703 alkoxides Chemical class 0.000 claims description 9
- 150000007942 carboxylates Chemical group 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 229920001451 polypropylene glycol Polymers 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical class O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 claims description 5
- 150000001340 alkali metals Chemical group 0.000 claims description 5
- 235000011056 potassium acetate Nutrition 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 4
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
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- 229940103091 potassium benzoate Drugs 0.000 claims description 3
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 claims description 3
- 239000001521 potassium lactate Substances 0.000 claims description 3
- 235000011085 potassium lactate Nutrition 0.000 claims description 3
- 229960001304 potassium lactate Drugs 0.000 claims description 3
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 claims description 3
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- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 239000004280 Sodium formate Substances 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 2
- 235000019254 sodium formate Nutrition 0.000 claims description 2
- 229920000582 polyisocyanurate Polymers 0.000 abstract description 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 57
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 43
- -1 alkali metal carboxylate Chemical class 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 150000002513 isocyanates Chemical class 0.000 description 25
- 235000013877 carbamide Nutrition 0.000 description 24
- 239000004202 carbamide Substances 0.000 description 23
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 238000007711 solidification Methods 0.000 description 19
- 230000008023 solidification Effects 0.000 description 19
- 150000005846 sugar alcohols Polymers 0.000 description 16
- 125000003368 amide group Chemical group 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 12
- PGYPOBZJRVSMDS-UHFFFAOYSA-N loperamide hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N(C)C)CCN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 PGYPOBZJRVSMDS-UHFFFAOYSA-N 0.000 description 12
- 239000002131 composite material Substances 0.000 description 11
- 239000000835 fiber Substances 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000002023 wood Substances 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000011324 bead Substances 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 5
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 5
- 238000006735 epoxidation reaction Methods 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
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- 150000003512 tertiary amines Chemical class 0.000 description 4
- WWIYWFVQZQOECA-UHFFFAOYSA-M tetramethylazanium;formate Chemical compound [O-]C=O.C[N+](C)(C)C WWIYWFVQZQOECA-UHFFFAOYSA-M 0.000 description 4
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- GTACSIONMHMRPD-UHFFFAOYSA-N 2-[4-[2-(benzenesulfonamido)ethylsulfanyl]-2,6-difluorophenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=C(F)C=C1SCCNS(=O)(=O)C1=CC=CC=C1 GTACSIONMHMRPD-UHFFFAOYSA-N 0.000 description 3
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/16—Catalysts
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/08—Processes
- C08G18/089—Reaction retarding agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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EP12176644.8A EP2687551A1 (en) | 2012-07-17 | 2012-07-17 | Intermediate polyisocyanurate comprising materials |
PCT/EP2013/062597 WO2014012728A1 (en) | 2012-07-17 | 2013-06-18 | Intermediate polyisocyanurate comprising materials |
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CA2938666A1 (en) * | 2014-02-04 | 2015-08-13 | Atlas Roofing Corporation | Thermally stable rigid foams and methods of making same |
DE102015105053A1 (de) * | 2015-04-01 | 2016-10-06 | Airbus Operations Gmbh | Verfahren zum Verarbeiten eines Bauteils, Bauteil, Bauteileinheit und beschichtetes Bauteil |
KR20170139022A (ko) * | 2015-04-21 | 2017-12-18 | 코베스트로 도이칠란트 아게 | 단열성 조건 하에 제조된 폴리이소시아누레이트 중합체를 기재로 하는 고형물 |
BR112017026744B1 (pt) * | 2015-06-18 | 2022-03-29 | Huntsman International Llc | Sistema de poliisocianato reativo de 2 componentes para a formação de poliuretano, processo para preparação de um material compreendendo poliuretano, e, material compreendendo poliuretano |
KR102401314B1 (ko) * | 2016-05-18 | 2022-05-25 | 바스프 에스이 | 폴리이소시아누레이트 경질 폼의 제조 방법 |
EP3381962A1 (de) * | 2017-03-29 | 2018-10-03 | Covestro Deutschland AG | Erzeugung von polyisocyanuratschichten durch getrennte auftragung von isocyanatkomponenten und katalysatoren |
EP3728384B1 (de) * | 2017-12-21 | 2023-03-01 | Covestro Deutschland AG | Verfahren zur herstellung isocyanuratgruppen-haltiger isocyanat-mischungen |
US11702499B2 (en) | 2018-12-11 | 2023-07-18 | Trimer Technologies Llc | Polyisocyanurate based polymers and fiber reinforced composites |
MX2021006909A (es) | 2018-12-11 | 2021-10-13 | Trimer Tech Llc | Polímeros basados en poliisocianurato y compuestos reforzados con fibra. |
MX2022004946A (es) * | 2019-10-22 | 2022-07-13 | Trimer Tech Llc | Fabricacion de materiales compuestos reforzados con fibra con una resina de isocianato. |
US11453739B2 (en) * | 2020-06-16 | 2022-09-27 | Covestro Llc | Use of thermally decomposable acid as inhibitor for preparing polyisocyanurate composites |
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US5223551A (en) * | 1991-12-26 | 1993-06-29 | Uop | Urea-modified isocyanurates and method of making rigid foams thereof |
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DE1212546B (de) * | 1962-06-05 | 1966-03-17 | Bayer Ag | Verfahren zur Polymerisation von aromatischen Polyisocyanaten |
GB1192859A (en) * | 1967-12-28 | 1970-05-20 | Takeda Chemical Industries Ltd | A Stabilised Isocyanate Composition |
DE2403858A1 (de) | 1974-01-28 | 1975-08-21 | Basf Ag | Stabile, fluessige amid- und/oder acylharnstoffgruppenhaltige isocyanurat-polyisocyanatloesungen |
JPS5214692A (en) * | 1975-07-25 | 1977-02-03 | Mitsui Toatsu Chem Inc | Process for preparing an organic isocyanate polymer |
DE2712931A1 (de) | 1977-03-24 | 1978-09-28 | Veba Chemie Ag | Isocyanuratgruppen - und endstaendig- blockierte isocyanatgruppen - enthaltende verbindungen |
JPS53118498A (en) * | 1977-03-25 | 1978-10-16 | Mitsui Toatsu Chem Inc | One-can polyurethane composition |
US4284730A (en) | 1980-02-07 | 1981-08-18 | Basf Wyandotte Corporation | Liquid carbodiimide- and uretonimine-isocyanurate-containing polyisocyanate compositions and microcellular foams made therefrom |
JPS58145721A (ja) * | 1982-02-24 | 1983-08-30 | Hitachi Ltd | 樹脂組成物の硬化方法 |
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FR2579205B1 (fr) | 1985-03-25 | 1987-05-15 | Rhone Poulenc Spec Chim | Procede de preparation de polyisocyanates polyisocyanurates par cyclotrimerisation catalytique de polyisocyanates |
DE3627078A1 (de) * | 1986-08-09 | 1988-02-18 | Bayer Ag | Verfahren zur herstellung von formkoerpern auf polyurethan- und/oder polyharnstoff-basis und die nach diesem verfahren erhaltenen formkoerper |
US4743627A (en) | 1987-09-14 | 1988-05-10 | Basf Corporation | Liquid isocyanurate-modified polymethylene bis(phenylisocyanate) compositions containing a high two-ring methylene bis(phenylisocyanate) content |
JPH02110123A (ja) | 1988-10-19 | 1990-04-23 | Asahi Chem Ind Co Ltd | ポリイソシアナートの製法 |
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2013
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- 2013-06-18 CN CN201380038054.0A patent/CN104640892B/zh active Active
- 2013-06-18 BR BR112015001029-6A patent/BR112015001029B1/pt not_active IP Right Cessation
- 2013-06-18 WO PCT/EP2013/062597 patent/WO2014012728A1/en active Application Filing
- 2013-06-18 MX MX2015000620A patent/MX369050B/es active IP Right Grant
- 2013-06-18 JP JP2015522010A patent/JP2015528039A/ja active Pending
- 2013-06-18 RU RU2015105176A patent/RU2628086C2/ru active
- 2013-06-18 EP EP13730231.1A patent/EP2875059B1/en active Active
- 2013-06-18 KR KR1020157000881A patent/KR102005824B1/ko not_active Expired - Fee Related
- 2013-06-18 PL PL13730231T patent/PL2875059T3/pl unknown
- 2013-06-18 US US14/413,459 patent/US9631043B2/en active Active
- 2013-06-18 IN IN31DEN2015 patent/IN2015DN00031A/en unknown
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Publication number | Publication date |
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RU2015105176A (ru) | 2016-09-10 |
KR102005824B1 (ko) | 2019-08-01 |
JP2015528039A (ja) | 2015-09-24 |
TW201404792A (zh) | 2014-02-01 |
EP2875059B1 (en) | 2021-01-06 |
EP2875059A1 (en) | 2015-05-27 |
US20150158967A1 (en) | 2015-06-11 |
MX2015000620A (es) | 2015-04-14 |
EP2687551A1 (en) | 2014-01-22 |
CA2878797A1 (en) | 2014-01-23 |
WO2014012728A1 (en) | 2014-01-23 |
BR112015001029A2 (pt) | 2017-06-27 |
US9631043B2 (en) | 2017-04-25 |
IN2015DN00031A (enrdf_load_stackoverflow) | 2015-05-22 |
CA2878797C (en) | 2017-07-04 |
CN104640892A (zh) | 2015-05-20 |
MX369050B (es) | 2019-10-28 |
PL2875059T3 (pl) | 2021-08-23 |
RU2628086C2 (ru) | 2017-08-14 |
BR112015001029B1 (pt) | 2021-03-02 |
KR20150036063A (ko) | 2015-04-07 |
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